methyl 4-oxotetrahydrothiophene-3-carboxylate
methyl 4-oxotetrahydrothiophene-3-carboxylate
CAS: 2689-68-1
Molecular Formula: C6H8O3S
methyl 4-oxotetrahydrothiophene-3-carboxylate - Names and Identifiers
methyl 4-oxotetrahydrothiophene-3-carboxylate - Physico-chemical Properties
| Molecular Formula | C6H8O3S |
| Molar Mass | 160.19 |
| Density | 1.309±0.06 g/cm3(Predicted) |
| Melting Point | 37-38 °C |
| Boling Point | 95 °C |
| Solubility | Chloroform |
| Appearance | Solid |
| Color | Light Yellow |
| pKa | 10.52±0.20(Predicted) |
| Storage Condition | 2-8°C(protect from light) |
methyl 4-oxotetrahydrothiophene-3-carboxylate - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
| HS Code | 29339900 |
| Hazard Class | IRRITANT |
methyl 4-oxotetrahydrothiophene-3-carboxylate - Reference Information
| Introduction | methyl 4-oxotetrahydrothiophenol -3-carboxylate is an important organic intermediate, as it can be used to prepare 2-(ethylthio) thieno [3,4-d] pyrimidin-4-(3H,5h, 7h)-one, it can be prepared by reacting methyl acrylate with methyl mercaptoacetate. |
| preparation method | methyl 4-oxotetrahydrothiophenol -3-carboxylate was prepared as follows: 1) methyl acrylate (99.2, 1.1 mmol) was added slowly to a solution of methyl mercaptoacetate (91 mL, 1.0 mmol) and piperidine (2.0 mL, 0.02 mol) while maintaining the temperature of the reaction mixture at 50 °c. The reaction was stirred for 2 hours, then excess methyl acrylate and piperidine were distilled off under high vacuum to give the target product methyl 3-((methoxycarbonyl) methylthio) propionate (185g, 96%). LC-MS (method A):(ES +) 193,RT = 4.29 min. 2) lithium metal (250g, 2.12 mol) was treated with methanol (80 mL) in toluene (0.30 mL) at room temperature. After all the lithium was dissolved, methyl 3-((methoxycarbonyl) methylthio) propionate was added over 0.5 hours at 70 °c. The reaction temperature was then increased (methanol was distilled off) to a final temperature of 110 °c and this temperature was maintained for 18 hours. The resulting mixture contained a 1:1 mixture of the desired product and methyl 3-oxotetrahydrothiophene-2-carboxylate. The reaction was cooled and the solid was collected by filtration to provide a solid enriched with the desired product lithium salt. The solid was acidified with 1N HCl solution and extracted with DCM. The organic phase was concentrated and the residue was purified by column chromatography, eluting with EtOAc/petroleum ether (2 to 10%) to remove any residual methyl 3-oxotetrahydrothiophene-2-carboxylate, methyl 4-oxotetrahydrothiophenol -3-carboxylate (14.7g, 33%) was obtained from the second eluted fraction of the column. |
| EPA chemical substance information | information is provided by: ofmpeb.epa.gov (external link) |
Last Update：2024-04-09 20:49:11
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Product Name: Tetrahydro-4-oxo-3-thiophenecarboxylic Acid Methyl Ester Visit Supplier Webpage Request for quotationCAS: 2689-68-1
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Mobile: 18021002903
QQ: 3008007409
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